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Crystal forms of astaxanthin

a technology of astaxanthin and crystal forms, which is applied in the field of crystal forms comprising astaxanthin, can solve the problems that the administration of astaxanthin crystals in fish feed pellets and other nutritional dosage forms does not give sufficient oral uptake of colouran

Inactive Publication Date: 2009-07-21
PHARES PHARMA RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

"This patent describes a mixture of two new crystal forms of astaxanthin, designated as crystal Forms I and II, and methods for preparing them. The patent also describes the physical and solubility properties of these crystal forms. The technical effects of this patent include the creation of new crystal forms of astaxanthin with improved properties, such as increased solubility and stability. These new crystal forms can be used in various applications, such as in the preparation of solid compositions and in the preparation of physical forms of astaxanthin."

Problems solved by technology

Because of poor solubility in a physiological milieu, administration of astaxanthin crystals in fish feed pellets and other nutritional dosage forms does not give sufficient oral uptake of the colourant.

Method used

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  • Crystal forms of astaxanthin
  • Crystal forms of astaxanthin
  • Crystal forms of astaxanthin

Examples

Experimental program
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Effect test

example 1

[0177]40 mg of astaxanthin (97.2 mol % all-trans-astaxanthin and 1.6 mol % 9-cis-astaxanthin and 1.2 mol % 13-cis-astaxanthin) is dissolved in 2 ml dichloromethane (DCM) at 30° C. and processed into crystals by solvent removal under vacuum, Raman spectrum shows the presence of crystal Form II as in FIG. 4. The X-Ray diffraction pattern is shown in FIG. 3. HPLC analysis of the crystals show 99.2 mol % all-trans-astaxanthin, 0.4 mol % 9-cis-astaxanthin, 0.4 mol % 13-cis -astaxanthin, corresponding with a carotenoidal compound level of about 0.8 mol %.

example 2

[0178]20 mg analytical grade astaxanthin (97.2 mol % all-trans-astaxanthin and 1.6 mol % 9-cis-astaxanthin and 1.2 mol % 13-cis-astaxanthi) is dissolved in 1 ml pyridine and heated at 70° C. for 30 min. After addition of 8.0 ml cold water, the formed crystals are washed with water and the Raman spectrum shows the presence of crystal Form I as seen in the spectrum in FIG. 2. The X-Ray diffraction pattern is shown in FIG. 1. HPLC determination confirms the total amount of all-trans-astaxanthin and cis-astaxanthin isomers to be 100%. The astaxanthin comprises 78 mol % all-trans-astaxanthin, 3 mol % 9-cis-astaxantlhn and 19 mol % 13-cis-astaxanthin. The level of carotenoidal products is about 22 mol %. Similarly, when the pyridine solution is heated at 80° for 40 min, 28 mol % 13-cis -astaxanthin is formed and the resulting crystal is assigned as astaxanthin crystal Form I by the characteristic X-ray diffraction pattern and Raman spectrum.

example 3

[0179]20 mg of astaxanthin comprising 97.2 mol % all-trans-astaxanthin and 2.8 mol % cis-astaxant (further comprising 1.6 mol % 9-cis-astaxanthin and 1.2 mol % 13-cis-astaxant) is dissolved in 1.0 ml pyridine at room temperature (solution 1). 20 mg of astaxanthin from Example 2 comprising 72 mol % all-trans-astaxanthin and 28 mol % 13-cis-astaxantliin are dissolved in 1.0 ml pyridine at room temperature (solution 2). The two solutions are mixed at several ratios and 0.6 ml cold water is added, the formed crystals are collected by filtration, washed with 2 ml water and a Raman spectrum is recorded after drying. The results are summarized in Table 6.

[0180]

TABLE 6PreparationCarotenoidalcrystallization solutioncompound level inVolumeVolumecrystallizationSolution 1Solution 2solutionCrystal Form(μl)(μl)(mol %)III20003.000.01.020053.610.01.0200104.190.01.0200205.270.430.57200508.000.550.4520010011.330.70.320020015.501.00.06020022.231.00.02020025.771.00.0020028.001.00.0

[0181]Example 3 clear...

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Abstract

Mixtures of specific crystal forms of astaxanthin and the individual crystal forms designated crystal Form I and II and disclosed together with methods for preparing said crystal Forms. Methods for preparing nutritional dosage forms including the disclosed astaxanthin crystal forms for the life science industry are also disclosed.

Description

RELATED APPLICATIONS[0001]This application claims priority under 35 U.S.C. §119 to European Patent Application 05 017 709.6 filed in Europe on Aug. 15, 2005, and as a continuation application under 35 U.S.C. §120 to PCT / EP2006 / 008047 filed as an International Application on Aug. 15, 2006 designating the U.S., the entire contents of which are hereby incorporated by reference in their entireties.TECHNICAL FIELD[0002]This disclosure relates to crystal forms comprising astaxanthin and to related processes, compositions and methods.BACKGROUND INFORMATION[0003]Delivering a colourant such as astaxanthin with good oral bioavailability for improved plasma uptake and flesh deposition in salmonid is a particular concern for fish feed producers and fish farmers. Because of poor solubility in a physiological milieu, administration of astaxanthin crystals in fish feed pellets and other nutritional dosage forms does not give sufficient oral uptake of the colourant. In order to make the colourant m...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07C45/00
CPCC07C403/24A23K50/80
Inventor LEIGH, STEVELEIGH, MATHEW LOUIS STEVENVAN HOOGEVEST, PETER
Owner PHARES PHARMA RES